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1-Methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid

  • CAS No. 934568-20-4

  • Cat. No. CS-0004410
  • Purity≥96%
  • MDL No.MFCD11043031

*For research and further manufacturing use only, not for direct human use.

1-Methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid|CS-0004410

Structure of 934568-20-4

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General Information

  • CAS No. 934568-20-4
  • Cat. No. CS-0004410
  • Purity ≥96%
  • MDL No. MFCD11043031
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₈N₂O₂
  • Molecular Weight 176.17
  • Synonym(s) 1-Methyl-7-azaindole-5-carboxylic acid
  • SMILES O=C(O)C1=CN=C2N(C)C=CC2=C1

Description

1-Methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid features a rigid heteroaromatic core with a methylated pyrrolopyridine scaffold and a carboxylic acid handle. This structure combines enhanced solubility with electronic properties favorable for medicinal chemistry applications, enabling direct incorporation into bioactive molecules under standard coupling conditions.

Application

1-Methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid serves as a versatile building block for heterocyclic synthesis, enabling efficient access to fused pyrrole-pyridine scaffolds prevalent in medicinal chemistry. The carboxylic acid group facilitates direct derivatization via amide coupling, esterification, or decarboxylative functionalization, while the methylated pyrrole ring enhances stability and modulates electronic properties. Its bench-stable nature and compatibility with standard reaction conditions make it well-suited for iterative synthesis workflows and API intermediate development.

Synthesis

  • Route1
    • 1H-Pyrrolo[2,3-b]pyridine-5-carbonitrile, 1-methyl-|CS-0004058
      517918-96-6
    • ~97%
    • In-stock
      1-Methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid|CS-0004410
      934568-20-4

    References

    • Harrison, Scott T.; Mulhearn, James; Wolkenberg, Scott E.; Miller, Patricia J.; O'Malley, Stacey S.; Zeng, Zhizhen; Williams Jr., David L.; Hostetler, Eric D.; Sanabria-Bohorquez, Sandra; Gammage, Linda; Fan, Hong; Sur, Cyrille; Culberson, J. Christopher; Hargreaves, Richard J.; Cook, Jacquelynn J.; Hartman, George D.; Barrow, James C. ACS Medicinal Chemistry Letters, 2011 , vol. 2, # 7 p. 498 - 502
  • Route2
    • 1H-Pyrrolo[2,3-b]pyridine-5-carboxylic acid, 1-methyl-, methyl ester|CS-0004409
      934568-21-5
    • ~%
    • In-stock
      1-Methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid|CS-0004410
      934568-20-4

    References

    • ADVINUS THERAPEUTICS LIMITED; KHARUL, Rajendra; BHUNIYA, Debnath; MOOKHTIAR, Kasim A.; SINGH, Umesh; HAZARE, Atul; PATIL, Satish; DATRANGE, Laxmikant; THAKKAR, Mahesh Patent: WO2013/42139 A1, 2013 ; Location in patent: Page/Page column 75-76 ;
  • Route3

    References

    • Harrison, Scott T.; Mulhearn, James; Wolkenberg, Scott E.; Miller, Patricia J.; O'Malley, Stacey S.; Zeng, Zhizhen; Williams Jr., David L.; Hostetler, Eric D.; Sanabria-Bohorquez, Sandra; Gammage, Linda; Fan, Hong; Sur, Cyrille; Culberson, J. Christopher; Hargreaves, Richard J.; Cook, Jacquelynn J.; Hartman, George D.; Barrow, James C. ACS Medicinal Chemistry Letters, 2011 , vol. 2, # 7 p. 498 - 502

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362-P405-P501

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Computational Chemistry Data

  • TPSA   55.12
  • LogP   1.2715
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   1

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